Phenylbenzamides

ABSTRACT

This invention relates to novel phenylbenzamides of the formula (I) 
                         
in which
         R 1  represents trifluoromethyl, chlorine, bromine or iodine and   R 2  represents hydrogen, methyl or ethyl,
 
to a process for preparing these substances and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP2003/006512, filed Jun. 20, 2003,which was published in German as International Patent Publication WO2004/005242 on Jan. 15, 2004, which is entitled to the right of priorityof German Patent Application 102 29 595.6, filed Jul. 2, 2002.

The present invention relates to novel phenylbenzamides, to a processfor their preparation and to their use for controlling unwantedmicroorganisms.

It is already known that numerous phenylbenzamides have fungicidalproperties (cf., for example, EP-A 0 545 099). Thus, for example, thephenylbenzamides N-(2-hexylphenyl)-2-(trifluoromethyl)benzamide andN-(2-hexylphenyl)-2-iodobenzamide are already known from EP-A 0 545 099,but the patent application mentioned does not contain any data on theirbiological activity.

There have now been found novel phenylbenzamides of the formula (I)

in which

-   R¹ represents trifluoromethyl, chlorine, bromine or iodine and-   R² represents hydrogen or methyl,-   R² furthermore represents ethyl.

Furthermore, it has been found that the phenylbenzamides of the formula(I) are obtained when

-   a) in a first step, aniline is reacted with an alkene of the formula    (II)

-   -   in which    -   R² represents hydrogen or methyl,    -   R² furthermore represents ethyl,    -   in the presence of a base and in the presence of a Lewis acid,        and the resulting alkylphenylamine derivative of the formula        (III)

-   -   in which    -   R² represents hydrogen or methyl,    -   R² furthermore represents ethyl,

-   b) is, in a second step reacted with a benzoyl chloride of the    formula (IV)

-   -   in which    -   R¹ represents trifluoromethyl, chlorine, bromine or iodine,    -   if appropriate in the presence of an acid binder and if        appropriate in the presence of a diluent.

Finally, it has been found that the novel phenylbenzamides of theformula (I) have very good microbicidal properties and can be used forcontrolling unwanted microorganisms both in crop protection and in theprotection of materials.

Surprisingly, the phenylbenzamides of the formula (I) according to theinvention have considerably better fungicidal activity than theconstitutionally most similar active compounds of the prior art havingthe same direction of action.

The formula (I) provides a general definition of the phenylbenzamidesaccording to the invention.

Preference is given to phenylbenzamides of the formula (I) in which R²represents hydrogen.

Preference is given to phenylbenzamides of the formula (I) in which R²represents methyl.

Preference is given to phenylbenzamides of the formula (I) in which R²represents ethyl.

Preference is given to phenylbenzamides of the formula (I) in which R¹represents tri-fluoromethyl or iodine.

According to the invention, the formula (I) embraces the followingphenylbenzamides:

-   N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide,-   N-[2-(1,3-dimethylbutyl)phenyl]-2-chlorobenzamide,-   N-[2-(1,3-dimethylbutyl)phenyl]-2-bromobenzamide,-   N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide,-   2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,-   2-chloro-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,-   2-bromo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,-   2-iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,-   [2-(trifluoromethyl)phenyl]-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide,-   (2-chlorophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide,-   (2-bromophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide,-   (2-iodophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide.

Using aniline, 4-methyl-1-pentene and 2-(trifluoromethyl)benzoylchloride as starting materials, the course of the process according tothe invention can be illustrated by the following formula scheme:

The components aniline and the alkenes of the formula (II), that is4-methyl-1-pentene, 4,4-dimethyl-1-pentene and 4,4-dimethyl-1-hexene,required as starting materials for carrying out the first step of theprocess according to the invention are generally known chemicals forsynthesis and commercially available.

The benzoyl chlorides of the formula (IV), that is2-(trifluoromethyl)benzoyl chloride, 2-chlorobenzoyl chloride,2-bromobenzoyl chloride and 2-iodobenzoyl chloride, required as startingmaterials for carrying out the second step of the process according tothe invention are generally known chemicals for synthesis andcommercially available.

The alkylphenylamine derivatives of the formula (III) obtained in thefirst step (a) of the process according to the invention are novel andalso form part of the subject-matter of the present invention.

The alkylphenylamine derivatives of the formula (III) according to theinvention are 2-(1,3-dimethylbutyl)phenylamine,2-(1,3,3-trimethylbutyl)phenylamine and2-(1,3,3-trimethylpentyl)phenylamine.

Suitable bases for carrying out the first step (a) of the processaccording to the invention are all inorganic and organic bases customaryfor such reactions. Preference is given to using aluminium granules (cfDE-A 27 30 620).

Suitable Lewis acids for carrying out the first step (a) of the processaccording to the invention are all compounds customary for suchreactions. Preference is given to using aluminium chloride or ironchloride, particularly preferably aluminium chloride (cf. DE-A 27 30620).

Suitable acid binders for carrying out the second step (b) of theprocess according to the invention are all inorganic and organic basescustomary for such reactions. Preference is given to using alkalineearth metal or alkali metal hydroxides, such as sodium hydroxide,calcium hydroxide, potassium hydroxide or else ammonium hydroxide,alkali metal carbonates, such as sodium carbonate, potassium carbonate,potassium bicarbonate, sodium bicarbonate, alkali metal or alkalineearth metal acetates, such as sodium acetate, potassium acetate, calciumacetate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).Particular preference is given to using potassium carbonate.

Suitable diluents for carrying out the second step (b) of the processaccording to the invention are all customary inert organic solvents.Preference is given to using optionally halogenated aliphatic, alicyclicor aromatic hydrocarbons, such as petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbontetrachloride, dichloroethane or trichloroethane; ethers, such asdiethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethaneor anisol; nitrites, such as acetonitrile, propionitrile, n- ori-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate; sulphoxides, such as dimethyl sulphoxide; or sulphones, such assulpholane. Particular preference is given to using acetonitrile.

When carrying out the first step (a) of the process according to theinvention, the reaction temperatures can in each case be varied within arelatively wide range. In general, the first step is carried out attemperatures between 100° C. and 300° C., preferably between 150° C. and280° C., particularly preferably between 200° C. and 260° C.

The process according to the invention is generally in each case carriedout under elevated pressure of from 1 bar to 250 bar. The operations arepreferably carried out under elevated pressure of from 50 bar to 150bar.

When carrying out the second step (b) of the process according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the second step is carried out at temperaturesbetween −20° C. and 180° C., preferably between 10° C. and 50° C.

The second step (b) of the process according to the invention isgenerally in each case carried out under atmospheric pressure. However,in each case it is also possible to operate under elevated or reducedpressure.

When carrying out the first step (a) of the process according to theinvention, in general from 1 to 10 mol, preferably from 1.5 to 5 mol,particularly preferably from 2 to 2.5 mol, of 4-methyl-1-pentene areemployed per mole of aniline. However, it is also possible to employ thereaction components in other ratios. Work-up is carried out by customarymethods. In general, the reaction mixture is stirred with toluene andaqueous base, and the organic phase is separated off and, after drying,concentrated under reduced pressure. The residue that remains may, ifrequired, be freed of any impurities that may still be present usingcustomary methods, such as chromatography, distillation orrecrystallization.

When carrying out the second step (b) of the process according to theinvention, in general 1 mol or else an excess of2-(1,3-dimethylbutyl)phenylamine of the formula (II) is employed permole of benzoyl chloride of the formula (III). However, it is alsopossible to employ the reaction components in other ratios. Work-up iscarried out by customary methods. In general, the reaction mixture isextracted with water and the organic phase is separated off, dried andconcentrated under reduced pressure. The residue that remains may, ifrequired, be freed of any impurities that may still be present usingcustomary methods, such as chromatography or recrystallization.

The substances according to the invention have potent microbicidalactivity and can be employed for controlling unwanted microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

-   Xanthomonas species, such as, for example, Xanthomonas campestris    pv. oryzae;-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Pythium species, such as, for example, Pythium ultimum;-   Phytophthora species, such as, for example, Phytophthora infestans;-   Pseudoperonospora species, such as, for example, Pseudoperonospora    humuli or Pseudoperonospora cubensis;-   Plasmopara species, such as, for example, Plasmopara viticola;    Bremia species, such as, for example, Bremia lactucae;-   Peronospora species, such as, for example, Peronospora pisi or P.    brassicae;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Botrytis species, such as, for example, Botrytis cinerea;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae; and-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

The active compounds according to the invention also have very goodfortifying action in plants. Accordingly, they can be used formobilizing the defences of the plant against attack by unwantedmicroorganisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defence system of plants such that, when thetreated plants are subsequently inoculated with unwanted microorganisms,they show substantial resistance against these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

At certain concentrations and application rates, the active compoundsaccording to the invention can also be used as herbicides, forinfluencing plant growth and for controlling animal pests. They can alsobe used as intermediates and precursors for the synthesis of furtheractive compounds.

The active compounds according to the invention can be used to treat allplants and parts of plants. By plants are understood here all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding the plant varieties which can or cannot be protected byvarietal property rights. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, trunks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and the parts of plants with the activecompounds according to the invention is carried out directly or byaction on their surroundings, habitat or storage space, according tocustomary treatment methods, for example by dipping, spraying,evaporating, atomizing, broadcasting, spreading-on and, in the case ofpropagation material, in particular in the case of seeds, furthermore byone- or multi-layer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes), and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis,-   Aspergillus, such as Aspergillus niger,-   Chaetomium, such as Chaetomium globosum,-   Coniophora, such as Coniophora puetana,-   Lentinus, such as Lentinus tigrinus,-   Penicillium, such as Penicillium glaucum,-   Polyporus, such as Polyporus versicolor,-   Aureobasidium, such as Aureobasidium pullulans,-   Sclerophoma, such as Sclerophoma pityophila,-   Trichoderma, such as Trichoderma viride,-   Escherichia, such as Escherichia coli,-   Pseudomonas, such as Pseudomonas aeruginosa, and-   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing components are the following:

Fungicides:

-   2-phenylphenol; 8-hydroxyquinolin sulphate;-   acibenzolar-5-methyl; aldimorph; amidoflumet; ampropylfos;    ampropylfos-potassium; andoprim; anilazine; azaconazole;    azoxystrobin;-   benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl;    benzamacril; benzamacril-isobutyl; bilanafos; binapacryl; biphenyl;    bitertanol; blasticidin-S; bromuconazole; bupirimate; buthiobate;    butylamine;-   calcium polysulphide; capsimycin; captafol; captan; carbendazim;    carboxin; carpropamid; carvone; chinomethionat; chlobenthiazone;    chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon;    cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil;    cyprofuram;-   Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;    diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole;    diflumetorim; dimethirimol; dimethomorph; dimoxystrobin;    diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione;    ditalimfos; dithianon; dodine; drazoxolon;-   edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;-   famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole;    fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil;    fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzinine;    fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin;    fluquinconazole; flurprimidol; flusilazole; flusulfamide;    flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium;    fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox;-   guazatine; hexachlorobenzene; hexaconazole; hymexazole;-   imazalil; imibenconazole; iminoctadine triacetate; iminoctadine    tris(albesil); iodocarb; ipconazole; iprobenfos; iprodione;    iprovalicarb; irumamycin; isoprothiolane; isovaledione;-   kasugamycin; kresoxim-methyl;-   mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl;    metalaxyl-M; metconazole; methasulfocarb; methfuroxam; metiram;    metominostrobin; metsulfovax; mildiomycin; myclobutanil; myclozolin;-   natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol;-   ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;    oxycarboxin; oxyfenthiin;-   paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen;    phthalide; picoxystrobin; piperalin; polyoxins; polyoxorim;    probenazole; prochloraz; procymidone; propamocarb;    propanosine-sodium; propiconazole; propineb; proquinazid;    prothioconazole; pyraclostrobin; pyrazophos; pyrifenox;    pyrimethanil; pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole;    quinoxyfen; quintozene;-   simeconazole; spiroxamine; sulphur;-   tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole;    thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram;    tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenol;    triazbutil; triazoxide; tricyclamide; tricyclazole; tridemorph;    trifloxystrobin; triflumizole; triforine; triticonazole;-   uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide;-   (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;-   1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;-   2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;-   2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;-   3,4,5-trichloro-2,6-pyridinedicarbonitrile;-   actinovate;-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;    monopotassium carbonate;-   N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;-   N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine;-   sodium tetrathiocarbonate;    and copper salts and preparations, such as Bordeaux mixture; copper    hydroxide; copper naphthenate; copper oxychloride; copper sulphate;    cufraneb; copper oxide; mancopper; oxine-copper.    Bactericides:-   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/Acaricides/Nematicides:-   abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,    aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin,    AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,    azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,    bifenazate, bifenthrin, bioethanomethrin, biopermethrin,    bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,    butocarboxim, butylpyridaben,-   cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan,    cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,    chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,    chlovaporthrin, chromafenozide, cisresmethrin, cispermethrin,    clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,    cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,    cypermethrin, cyromazine,-   deltamethrin, demeton M, demeton S, demeton-5-methyl, diafenthiuron,    diazinon, dichlorvos, dicofol, diflubenzuron, dimethoat,    dimethylvinphos, diofenolan, disulphoton, docusat-sodium, dofenapyn,-   eflusilanate, emamectin, empenthrin, endosulphan, Entomopfthora    spp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,    etoxazole, etrimfos, fenamiphos, fenazaquin, fenbutatin oxide,    fenitrothion, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin,    fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil,    fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,    flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophos,    fosmethilan, fosthiazate, fubfenprox, furathiocarb,-   granulosis viruses,-   halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,    hydroprene, imidacloprid, indoxacarb, isazofos, isofenphos,    isoxathion, ivennectin, nuclear polyhedrosis viruses,-   lambda-cyhalothrin, lufenuron,-   malathion, mecarbam, metaldehyde, methamidophos, Metharhizium    anisopliae, Metharhizium flavoviride, methidathion, methiocarb,    methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,    mevinphos, milbemectin, milbemycin, monocrotophos,-   naled, nitenpyram, nithiazine, novaluron, omethoate, oxamyl,    oxydemethon M,-   Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,    phenthoate, phorat, phosalone, phosmet, phosphamidon, phoxim,    pirmicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,    propargite, propoxur, prothiofos, prothoat, pymetrozine, pyraclofos,    pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,    pyriproxyfen,-   quinalphos, ribavirin,-   salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulphotep,    sulprofos,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,    tetrachlorvinphos, tetradifon thetacypermethrin, thiacloprid,    thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,    thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,    triarathene, triazamate, triazophos, triazuron, trichlophenidine,    trichlorfon, triflumuron, trimethacarb,-   vamidothion, vaniliprole, Verticillium lecanii,-   YI 5302, Zeta-cypermethrin, Zolaprofos-   (1R-cis)-[5-(phenylmethyl)-3-furanyl]methyl    3-[(dihydro-2-oxo-3(2H)-furanylidene)methyl]-2,2-dimethylcyclopropanecarboxylate,-   (3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropanecarboxylate,-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydrooxazole,-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)phenyl]amino]carbonyl]benzamide,-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]-benzamide,-   3-methylphenyl propylcarbamate-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene,-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyrida    4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,-   Bacillus thuringiensis strain EG-2348,-   [2-benzoyl-1-(1,1-dimethylethyl)hydrazinobenzoic acid,-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate,-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]cyanamide,-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)carboxaldehyde,-   ethyl[2-[[1,6-dihydro-6-oxo-1-(phenyhnethyl)-4-pyridazinyl]oxy]ethyl]carbamate,-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)glycine,-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitroguanidine,-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,-   O,O-diethyl[2-(dipropylamino)-2-oxoethyl]ethylphosphoramidothioate,-   N-cyanomethyl-4-trifluoromethylnicotinamide,-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridine-2-yloxy)propoxy]benzene.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi, (for example against Candida species,such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes, Microsporon species such as Microsporon canis andaudouinii. The list of these fungi by no means limits the mycoticspectrum covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts with active compounds according to the invention. In a preferredembodiment, wild plant species and plant cultivars, or those obtained byconventional biological breeding, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulphonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula (I)according to the invention or the active compound mixtures according tothe invention. The preferred ranges stated above for the activecompounds or mixtures also apply to the treatment of these plants.Particular emphasis is given to the treatment of plants with thecompounds and mixtures specifically mentioned in the present text.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1 Preparation of2-(1,3-dimethylbutyl)phenylamine of the formula (III)

In a steel autoclave, a mixture of 62.8 g (0.67 mol) of aniline, 132.8 g(1.58 mol) of 4-methylpent-1-ene, 1.82 g of aluminium granules and 5.58g (41.8 mmol) of aluminium chloride is heated to 255° C. The reactionmixture is kept at this temperature and under autogenous pressure for 10h.

For work-up, the contents of the autoclave are, after cooling andventing, transferred quantitatively into a new vessel using toluene, andstirred with 80 ml of 40% strength aqueous sodium hydroxide solution and100 ml of water at 30-40° C. for 15 min. The organic phase is separatedoff, washed with water and dried over potassium carbonate. The tolueneis removed using a rotary evaporator and the residue is then subjectedto fractional distillation.

This gives 43.9 g (33%) of 2-(1,3-dimethylbutyl)phenylamine as acolourless oil (boiling range 73-85° C., 0.3 mbar).

Example 2 N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide

5.32 g (30 mmol) of 2-(1,3-dimethylbutyl)phenylamine (Example 1) and6.26 g (30 mmol) of 2-(trifluoromethyl)benzoyl chloride are addeddropwise to a suspension of 4.15 g of potassium carbonate in 200 ml ofacetonitrile. The reaction mixture is stirred for 10 h.

For work-up, 200 ml of water are added to the reaction solution, and themixture is extracted with ethyl acetate. The organic phases are driedwith sodium sulphate and concentrated. The residue is chromatographed onsilica gel (gradient cyclohexane 100% to cyclohexane/ethyl acetate 1:4).

This gives 5.00 g (46%) ofN-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide of logP (pH2.3)=4.09.

Example 3 N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide

3.55 g (20 mmol) of 2-(1,3-dimethylbutyl)phenylamine (Example 1) and5.33 g (20 mmol) of 2-iodobenzoyl chloride are added dropwise to asuspension of 2.76 g of potassium carbonate in 100 ml of acetonitrile.The reaction mixture is stirred for 10 h.

For work-up, 100 ml of water are added to the reaction solution, and themixture is extracted with ethyl acetate. The organic phases are driedwith sodium sulphate and concentrated. The residue is chromatographed onsilica gel (gradient cyclohexane 100% to cyclohexane/ethyl acetate 1:4).

This gives 7.00 g (83%) ofN-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide of logP (pH 2.3)=4.12.

Analogously to the examples mentioned above, the following compounds areobtained starting with aniline and 4-methylpent-1-ene and2-chlorobenzoyl chloride and 2-bromobenzoyl chloride, respectively:

Example 4 N-[2-(1,3-dimethylbutyl)phenyl]-2-chlorobenzamide

[logP (pH 2.3)=3.98]

Example 5 N-[2-(1,3-dimethylbutyl)phenyl]-2-bromobenzamide

[logP (pH 2.3)=4.01]

Moreover, analogously to the examples mentioned above, the followingcompounds are obtained starting with aniline and 4,4-dimethyl-1-penteneand 2-(trifluoromethyl)benzoyl chloride, 2-chlorobenzoyl chloride,2-bromobenzoyl chloride and 2-iodobenzoyl chloride, respectively:

Example 62-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide

[logP (pH 2.3)=4.36]

Example 7 2-chloro-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide

[logP (pH 2.3)=4.25]

Example 8 2-bromo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide

[logP (pH 2.3)=4.29]

Example 9 2-iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide

[logP (pH 2.3)=4.40]

Example 10(2-iodophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide.

[logP (pH 2.3)=4.71]

Example 11[2-(trifluoromethyl)phenyl]-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide

[logP (pH 2.3)=4.68]

Example 12(2-chlorophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide.

[logP (pH 2.3)=4.60]

Example 13(2-bromophenyl)-N-[2-(1,3,3-trimethylpentyl)phenyl]carboxamide

[logP (pH 2.3)=4.63]

The logP values given in the Preparation Examples were determined inaccordance with EEC Directive 79/831 Annex V.A8 by HPLC (HighPerformance Liquid Chromatography) using a reversed-phase column (C 18).Temperature: 43° C.

Mobile phases for the determination in the acidic range: 0.1% aqueousphosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanols).

Use Examples

Example A

Sphaerotheca Test (Cucumber)/Protective

-   Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of    dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE A Sphaerotheca test (cucumber)/protective Application rate ofactive Efficacy Active compound compound in g/ha in %

100 100

100 100

Example B

Venturia Test (Apple)/Protective

-   Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of    dimethylacetamide-   Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whilst an efficacy of100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE B Venturia test (apple)/protective Application rate of activeEfficacy Active compound compound in g/ha in %

100 100

100 100

Example C

Botrytis Test (Bean)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, 2 small pieces of agar colonized by Botrytiscinerea are placed onto each leaf. The inoculated plants are placed in adark chamber at about 20° C. and 100% relative atmospheric humidity.

2 days after the inoculation, the size of the infected areas on theleaves is evaluated. 0% means an efficacy which corresponds to that ofthe control, whereas an efficacy of 100% means that no infection isobserved.

Active compounds, application rates and test results are shown in thetable below.

TABLE C Botrytis test (bean)/protective Application rate of activeEfficacy Active compound compound in g/ha in %

500 93

500 93

Example D

Alternaria Test (Tomato)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with an aqueous sporesuspension of Alternaria solani and then remain at 100% relativeatmospheric humidity for 24 hours. The plants are then kept at about 96%relative atmospheric humidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE D Alternaria test (tomato)/protective Application rate of activeEfficacy Active compound compound in g/ha in %

750 100

750 100

Example E

Erysiphe Test (Barley)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young cereal plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with spores of Erysiphegraminis f. sp. hordei. The plants are then placed in a greenhouse at70% relative atmospheric humidity and a temperature of 18° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE E Erysiphe test (barley)/protective Application rate of activeEfficacy Active compound compound in g/ha in %

750 95

750 95

Example F

Puccinia Test (Wheat)/Protective

-   Solvent: 25 parts by weight of N,N-dimethylacetamide-   Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are inoculated with aspore suspension of Puccinia recondita in a 0.1% strength aqueous agarsolution. After the spray coating has dried on, the plants are sprayedwith the preparation of active compound at the stated application rate.The plants remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 24 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE F Puccinia test (wheat)/protective Application rate of activecompound Efficacy Active compound in g/ha in %

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

Example G

Comparative Experiments

In the table below, the compounds according to the invention of examples

are compared to the following compounds, which are known from EP-A 0 545099:

The compounds were tested in comparative experiments according to useexamples A [Spaerotheca test (cucumber)/protective], D [Alternaria test(tomato)/protective] and E [Erysiphe test (barley)/protective].

In each case, the application rate was 500 ppm. The efficacy of theindividual compounds in the use examples in question is given in thetable below.

TABLE G Comparative experiments Example A Example D Example ESpaerotheca Alternaria Erysiphe test (cucumber) test (tomato) test(barley) Compound according to the protective protective protectiveinvention efficacy in % efficacy in % efficacy in % Ex.2

100 95 90 Ex.3

100 95 95 Ex.5

95 90 30 Comparative experiment Example A Example D Example ESpaerotheca Alternaria Erysiphe test (cucumber) test (tomato) test(barley) Compounds known protective protective protective from EP-A 0545 099 efficacy in % efficacy in % efficacy in % No. 6.3(p. 24)

10 0 10 No.14.3(p. 42)

0 0 0 No. 6.4(p. 24)

30 30 0 No.14.4(p. 42)

10 10 20 No. 6.9(p. 24)

0 0 0 No.14.9(p. 42)

0 0 0

1. A phenylbenzamide of formula (I)

in which R¹ represents trifluoromethyl, chlorine, bromine, or iodine, and R² represents hydrogen, methyl, or ethyl.
 2. A phenylbenzamide of formula (I) according to claim 1 in which R² represents hydrogen.
 3. A phenylbenzamide of formula (I) according to claim 1 selected from the group consisting of N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide, N-[2-(1,3-dimethylbutyl)phenyl]-2-chlorobenzamide, N-[2-(1,3-dimethylbutyl)phenyl]-2-bromobenzamide, N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide, 2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, 2-chloro-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, 2-bromo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, and 2-iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide.
 4. A process for preparing a phenylbenzamide of formula (I) according to claim 1 comprising (a) reacting aniline with an alkene of formula (II)

 in which R² represents hydrogen, methyl, or ethyl, in the presence of a base and in the presence of a Lewis acid to form an alkylphenylamine derivative of formula (III)

 in which R² represents hydrogen, methyl, or ethyl, and (b) reacting the alkylphenylamine derivative of formula (III) with a benzoyl chloride of formula (IV)

 in which R¹ represents trifluoromethyl, chlorine, bromine or iodine, optionally in the presence of an acid binder and optionally in the presence of a diluent.
 5. A composition for controlling fungi and bacteria in the protection of corps and materials comprising one or more phenylbenzamides of formula (I) according to claim 1 and one or more extenders and/or surfactants.
 6. A method for controlling fungi and bacteria that infects crops and materials comprising applying an effective amount of one or more phenylbenzamides of formula (I) according to claim 1 to the fungi and bacteria and/or their habitat.
 7. A process for preparing compositions for controlling fungi and bacteria that infects crops and materials comprising mixing one or more phenylbenzamides of formula (I) according to claim 1 with one or more extenders and/or surfactants.
 8. A process for preparing a phenylamine derivative of formula (III)

in which R² represents hydrogen, methyl, or ethyl, comprising reacting aniline with an alkene of formula (II)

in which R² represents hydrogen, methyl, or ethyl, in the presence of a base and in the presence of a Lewis acid.
 9. A method according to claim 6 wherein the fungi and bacteria are selected from Alternaria, Aspergillus, Chaetomium, Coniophora, Lentinus, Penicillium, Polyporus, Aureobasidium, Sclerophoma, Trichoderma, Escherichia, Pseudomonas, Staphylococcus, Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae, Streptomycetaceae, Xanthomonas, Pseudomonas, Erwinia, Pythium, Phytophthora, Pseudoperonospora, Plasmopara, Bremia, Peronospora, Erysiphe, Sphaerotheca, Podosphaera, Venturia, Pyrenophora, Cochliobolus, Uromyces, Puccinia, Sclerotinia, Tilletia, Ustilago, Pellicularia, Pyricularia, Fusarium, Botrytis, Septoria, Leptosphaeria, Cercospora, Alternaria, and Pseudocercosporella. 